Hailey Bieber Masters the Art of Effortless Cool in Vintage Gucci and The Row

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Hailey Bieber continues her reign as fashion’s undisputed queen of high-low dressing—effortless, intuitive, and always one step ahead of the trend.

Spotted in Los Angeles, the Rhode founder brought a touch of business casual polish to her signature laid-back aesthetic, blending vintage finds with luxury minimalism in that perfectly Hailey way. She paired a moss-green Christian Dior Sports sweatshirt—faded just enough to suggest a well-loved history—with a pair of dark-wash, low-rise Gap jeans. The casual combination felt nostalgic yet intentional, a wink to ’90s off-duty ease.

Then came the twist: flip-flops. But not just any pair—the shiny black leather version by The Row, famously understated and famously expensive. The contrast between her under-$100 jeans and four-figure sandals was peak Bieber—nonchalant sophistication with a knowing smirk.

The finishing touch elevated the entire look: a vintage Gucci Bamboo bag, pulled straight from the archives. Its structured, briefcase-like silhouette and curved bamboo handle channeled old-school Italian glamour, offering balance to her sporty, slouchy separates. A pair of classic black shades and loose waves added that final note of “just stepped out, but perfectly styled” insouciance.

With every appearance, Hailey proves her mastery lies not in trends but in the tension between polish and comfort. It’s business casual redefined—through the lens of a woman who makes a sweatshirt and flip-flops look like quiet luxury.

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